CA2808199C - Procedes permettant de produire des morphinones protegees en 3-o et des morphinone dienol carboxylates proteges en 3-o - Google Patents

Procedes permettant de produire des morphinones protegees en 3-o et des morphinone dienol carboxylates proteges en 3-o Download PDF

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Publication number
CA2808199C
CA2808199C CA2808199A CA2808199A CA2808199C CA 2808199 C CA2808199 C CA 2808199C CA 2808199 A CA2808199 A CA 2808199A CA 2808199 A CA2808199 A CA 2808199A CA 2808199 C CA2808199 C CA 2808199C
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CA
Canada
Prior art keywords
formula
compound
alkyl
chlorine
base
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Expired - Lifetime
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CA2808199A
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CA2808199A1 (fr
Inventor
Andreas Stumpf
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Euro Celtique SA
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Publication of CA2808199A1 publication Critical patent/CA2808199A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
    • C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Neurosurgery (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Neurology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pain & Pain Management (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biomedical Technology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Catalysts (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Steroid Compounds (AREA)
  • Saccharide Compounds (AREA)

Abstract

Les procédés décrits permettent de produire des aldéhydes et des cétones, qui consistent à faire réagir lalcool primaire ou secondaire correspondant en présence dacide trichloroisocyanurique, dun composé représenté par la formule R1SR2 et dune base. Dans un mode de réalisation, ledit alcool est un composé représenté par la formule (I), dans laquelle R3 est un groupe protecteur. On décrit également des procédés permettant de produire des morphines diénol carboxylates protégées en 3-O, qui consistent à permettre à un composé représenté par la formule (I) de soxyder en présence dun composé contenant du chlore et dun composé représenté par la formule R1SR2, et à faire réagir le produit de létape doxydation avec un agent dacylation.
CA2808199A 2004-02-06 2005-02-04 Procedes permettant de produire des morphinones protegees en 3-o et des morphinone dienol carboxylates proteges en 3-o Expired - Lifetime CA2808199C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US54271104P 2004-02-06 2004-02-06
US60/542,711 2004-02-06
CA2555215A CA2555215C (fr) 2004-02-06 2005-02-04 Procedes permettant de produire des morphinones protegees en 3-o et des morphinone dienol carboxylates proteges en 3-o

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA2555215A Division CA2555215C (fr) 2004-02-06 2005-02-04 Procedes permettant de produire des morphinones protegees en 3-o et des morphinone dienol carboxylates proteges en 3-o

Publications (2)

Publication Number Publication Date
CA2808199A1 CA2808199A1 (fr) 2005-08-25
CA2808199C true CA2808199C (fr) 2015-10-27

Family

ID=34860329

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2808199A Expired - Lifetime CA2808199C (fr) 2004-02-06 2005-02-04 Procedes permettant de produire des morphinones protegees en 3-o et des morphinone dienol carboxylates proteges en 3-o
CA2555215A Expired - Lifetime CA2555215C (fr) 2004-02-06 2005-02-04 Procedes permettant de produire des morphinones protegees en 3-o et des morphinone dienol carboxylates proteges en 3-o

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2555215A Expired - Lifetime CA2555215C (fr) 2004-02-06 2005-02-04 Procedes permettant de produire des morphinones protegees en 3-o et des morphinone dienol carboxylates proteges en 3-o

Country Status (33)

Country Link
US (6) US8003793B2 (fr)
EP (3) EP1711502B1 (fr)
JP (1) JP4963968B2 (fr)
KR (4) KR101011460B1 (fr)
CN (1) CN1918168B (fr)
AP (1) AP2006003716A0 (fr)
AT (2) ATE406372T1 (fr)
AU (1) AU2005212258B2 (fr)
BR (1) BRPI0506607B8 (fr)
CA (2) CA2808199C (fr)
CR (1) CR8590A (fr)
CY (2) CY1108506T1 (fr)
DE (2) DE602005018265D1 (fr)
DK (2) DK1711502T3 (fr)
EA (2) EA012905B1 (fr)
EC (1) ECSP066824A (fr)
ES (2) ES2313299T3 (fr)
GE (1) GEP20084454B (fr)
HR (2) HRP20080618T3 (fr)
IL (2) IL177281A (fr)
MA (1) MA28346A1 (fr)
MX (1) MXPA06008931A (fr)
NO (2) NO20063989L (fr)
NZ (2) NZ565355A (fr)
PL (2) PL1711502T3 (fr)
PT (2) PT1711502E (fr)
RS (2) RS50663B (fr)
SG (1) SG150500A1 (fr)
SI (2) SI1711502T1 (fr)
TN (1) TNSN06248A1 (fr)
UA (2) UA88646C2 (fr)
WO (1) WO2005077957A2 (fr)
ZA (1) ZA200606252B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL1711502T3 (pl) 2004-02-06 2009-02-27 Euro Celtique Sa Sposoby wytwarzania 3-o-zabezpieczonych morfinonów i karboksylanów 3-o-zabezpieczonych dienoli morfinonu
US8115002B2 (en) * 2006-09-20 2012-02-14 Mallinckrodt Llc Preparation of substituted morphinan-6-ones and salts and intermediates thereof
NZ579469A (en) * 2007-03-06 2011-02-25 Mallinckrodt Inc Process for the preparation of quaternary n-alkyl morphinan alkaloid salts
US9040726B2 (en) * 2007-03-06 2015-05-26 Mallinckrodt Llc Process for the preparation of quaternary N-alkyl morphinan alkaloid salts
EP2285780B1 (fr) * 2008-05-27 2015-08-26 Mallinckrodt LLC Procédés et composés pour la préparation de normorphinanes
US9458109B2 (en) * 2008-09-03 2016-10-04 Mallinckrodt Llc Substituted berbines and processes for their synthesis
CA2798884C (fr) 2010-05-10 2016-09-13 Euro-Celtique S.A. Fabrication de granules sans principe actif et comprimes les comprenant
AU2011252039B2 (en) 2010-05-10 2014-06-12 Euro-Celtique S.A. Pharmaceutical compositions comprising hydromorphone and naloxone
CN103002881B (zh) 2010-05-10 2015-09-02 欧洲凯尔特公司 载有活性剂的颗粒与额外活性剂的组合
WO2015071380A1 (fr) 2013-11-13 2015-05-21 Euro-Celtique S.A. Hydromorphone et naloxone utilisées pour le traitement de la douleur et du syndrome de dysfonctionnement intestinal dû aux opioïdes
US10351512B2 (en) 2015-09-30 2019-07-16 Fujifilm Wako Pure Chemical Corporation Method of producing organic compound

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2654756A (en) 1949-10-20 1953-10-06 Mallinckrodt Chemical Works Process of preparing codeinone, dihydrocodeinone, and dihydromorphinone
DE902257C (de) 1951-07-17 1954-01-21 Knoll Ag Verfahren zur Herstellung von Acylderivaten der Enolform des Codeinons
GB1495271A (en) * 1974-04-10 1977-12-14 Macfarlan Smith Ltd Dehydrohalogenation of codeinone derivatives
US4472253A (en) * 1981-08-17 1984-09-18 The Florida Board Of Regents On Behalf Of The Florida State University Process for the preparation of an N-substituted 3-O-alkyl-14-hydroxynormorphinone derivative
US5112975A (en) * 1984-03-27 1992-05-12 Mallinckrodt Specialty Chemicals Company Preparation of noroxymorphone from morphine
SE9003665D0 (sv) * 1990-11-16 1990-11-16 Kabivitrum Ab Morphine prodrugs
GB9116909D0 (en) * 1991-08-06 1991-09-18 Salford Ultrafine Chem & Res Morphine derivatives
US5821374A (en) * 1995-11-21 1998-10-13 Hoffmann-La Roche Inc. Process for the oxidation of alcohols
US5869669A (en) * 1996-07-26 1999-02-09 Penick Corporation Preparation of 14-hydroxynormorphinones from normorphinone dienol acylates
GB9713703D0 (en) * 1997-06-30 1997-09-03 Johnson Matthey Plc Preparation of opiates
US6177567B1 (en) * 1999-10-15 2001-01-23 Boehringer Ingelheim Chemicals, Inc. Method for preparing oxycodone
US6596877B2 (en) * 2001-10-17 2003-07-22 Novartis Ag Accelerated process for preparing O-methyl phenols, N-methyl heteroaromatic compounds, and methylated aminophenols
PL1711502T3 (pl) 2004-02-06 2009-02-27 Euro Celtique Sa Sposoby wytwarzania 3-o-zabezpieczonych morfinonów i karboksylanów 3-o-zabezpieczonych dienoli morfinonu

Also Published As

Publication number Publication date
MA28346A1 (fr) 2006-12-01
NZ565355A (en) 2008-09-26
EA200601394A1 (ru) 2006-12-29
US20120022259A1 (en) 2012-01-26
US20140171643A1 (en) 2014-06-19
US20170233400A1 (en) 2017-08-17
MXPA06008931A (es) 2007-01-26
IL205596A (en) 2011-11-30
DK1711502T3 (da) 2008-12-01
EP2194059A2 (fr) 2010-06-09
AU2005212258A1 (en) 2005-08-25
US20150239898A1 (en) 2015-08-27
CA2555215A1 (fr) 2005-08-25
CA2808199A1 (fr) 2005-08-25
WO2005077957A3 (fr) 2006-05-04
EA200801811A1 (ru) 2008-12-30
GEP20084454B (en) 2008-08-10
CN1918168A (zh) 2007-02-21
BRPI0506607A (pt) 2007-05-02
HK1119160A1 (en) 2009-02-27
CY1109838T1 (el) 2014-09-10
DE602005009321D1 (de) 2008-10-09
SI1864987T1 (sl) 2010-04-30
HK1103071A1 (en) 2007-12-14
US9670218B2 (en) 2017-06-06
US8003793B2 (en) 2011-08-23
EA016062B1 (ru) 2012-01-30
RS51317B (sr) 2010-12-31
KR20070026401A (ko) 2007-03-08
RS50663B (sr) 2010-06-30
PT1711502E (pt) 2008-11-20
DK1864987T3 (da) 2010-04-12
EP2194059A3 (fr) 2010-09-22
ZA200606252B (en) 2007-11-28
TNSN06248A1 (fr) 2007-12-03
KR100921696B1 (ko) 2009-10-15
PL1864987T3 (pl) 2010-05-31
IL177281A (en) 2012-02-29
NO20063989L (no) 2006-10-31
IL177281A0 (en) 2006-12-10
PL1711502T3 (pl) 2009-02-27
WO2005077957A2 (fr) 2005-08-25
EP1864987B1 (fr) 2009-12-09
SI1711502T1 (sl) 2009-02-28
EP1864987A3 (fr) 2008-02-20
ECSP066824A (es) 2006-12-29
UA87833C2 (uk) 2009-08-25
BRPI0506607B1 (pt) 2018-01-16
CR8590A (es) 2007-07-19
DE602005018265D1 (de) 2010-01-21
NZ548786A (en) 2008-08-29
EP1711502A2 (fr) 2006-10-18
ES2313299T3 (es) 2009-03-01
EP1864987A2 (fr) 2007-12-12
AP2006003716A0 (en) 2006-08-31
KR20070108956A (ko) 2007-11-13
NO20150276L (no) 2006-10-31
ATE451374T1 (de) 2009-12-15
EA012905B1 (ru) 2010-02-26
KR101011460B1 (ko) 2011-01-28
JP2007520563A (ja) 2007-07-26
ES2338054T3 (es) 2010-05-03
AU2005212258B2 (en) 2008-05-22
US20120225902A1 (en) 2012-09-06
NO339083B1 (no) 2016-11-14
CN1918168B (zh) 2011-04-27
CY1108506T1 (el) 2014-04-09
HRP20080618T3 (hr) 2009-01-31
PT1864987E (pt) 2010-03-09
US8685996B2 (en) 2014-04-01
ATE406372T1 (de) 2008-09-15
KR20090089486A (ko) 2009-08-21
HRP20100123T1 (hr) 2010-04-30
KR100921695B1 (ko) 2009-10-15
JP4963968B2 (ja) 2012-06-27
UA88646C2 (uk) 2009-11-10
SG150500A1 (en) 2009-03-30
CA2555215C (fr) 2013-05-21
KR20070117701A (ko) 2007-12-12
BRPI0506607B8 (pt) 2021-05-25
US20080146804A1 (en) 2008-06-19
EP1711502B1 (fr) 2008-08-27
US8198444B2 (en) 2012-06-12
US8975257B2 (en) 2015-03-10

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Effective date: 20130301